After Vermont became the fourteenth state, Chipman became a leader of its Federalist Party. In addition to his legal and political work, Chipman authored several works on government and law, and was a satirical poet.

On February 9, 1791, Chipman met with President George Washington to notify him officially of Vermont's decision to apply for admission to the Union as the 14th state.[2] New York had long objected to the existence of the government of Vermont on the grounds that Vermont was part of New York, a position that dated back to a pre-Revolutionary War dispute between the colonial governors of New York and New Hampshire over the right to sell Vermont land grants.[3] In 1790 New York agreed to give up its claim provided only that an agreement on the boundary between Vermont and New York could be concluded and that Congress would admit Vermont to the Union. Vermont's negotiators insisted on also settling the real-estate disputes rather than leaving those to be decided later in a federal court. (Before Vermont's admission, federal courts had no power in Vermont since Vermont's government held that Vermont was not a part of the United States.) Vermont paid $30,000 to settle the claims (about $800,000 in 2015).[4] On February 18 Congress decided to admit Vermont to the Union, effective March 4.[5]

Chipman was elected as a Federalist to the U.S. Senate to fill the vacancy caused by the resignation of Isaac Tichenor and served from October 17, 1797, until March 3, 1803;[7] he was an unsuccessful candidate for reelection. From 1806 to 1811 he was a member of the Vermont House of Representatives. In 1813 he was a member of the Vermont Council of Censors, the predecessor of the Vermont State Senate, which met periodically to review state statutes and ensure that they complied with the state constitution, and to propose constitutional amendments. Chipman was again chief justice of Vermont from 1813 to 1815, and was succeeded by Asa Aldis.[8] He was a professor of law at Middlebury College beginning in 1816.[9]

Jeffrey Chipman was a Justice of the Peace in Canandaigua, New York in the 1820s, and was the jurist from whom those attempting to prevent William Morgan from publishing a book opposing Freemasonry obtained an arrest warrant for Morgan, which eventually led to Morgan's disappearance and presumed death and the founding of the Anti-Masonic Party.[12]

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